EP3829305A1 - Use of a cationic polysaccharide compound as a fungicide, pesticide, algaecide, dessicant and for extending the shelf life of fruits and vegetables - Google Patents
Use of a cationic polysaccharide compound as a fungicide, pesticide, algaecide, dessicant and for extending the shelf life of fruits and vegetablesInfo
- Publication number
- EP3829305A1 EP3829305A1 EP19746475.3A EP19746475A EP3829305A1 EP 3829305 A1 EP3829305 A1 EP 3829305A1 EP 19746475 A EP19746475 A EP 19746475A EP 3829305 A1 EP3829305 A1 EP 3829305A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- spp
- polysaccharide compound
- cationic
- group
- use according
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- -1 cationic polysaccharide compound Chemical class 0.000 title claims abstract description 101
- 229920001282 polysaccharide Polymers 0.000 title claims abstract description 74
- 239000005017 polysaccharide Substances 0.000 title claims abstract description 73
- 239000000575 pesticide Substances 0.000 title claims abstract description 8
- 239000003619 algicide Substances 0.000 title claims abstract description 7
- 239000000417 fungicide Substances 0.000 title claims abstract description 7
- 230000000855 fungicidal effect Effects 0.000 title claims description 7
- 235000012055 fruits and vegetables Nutrition 0.000 title abstract description 6
- 229920002670 Fructan Polymers 0.000 claims description 45
- 125000002091 cationic group Chemical group 0.000 claims description 27
- 235000013399 edible fruits Nutrition 0.000 claims description 24
- 150000002772 monosaccharides Chemical group 0.000 claims description 19
- 150000004676 glycans Chemical class 0.000 claims description 16
- 235000013311 vegetables Nutrition 0.000 claims description 14
- 239000007921 spray Substances 0.000 claims description 13
- 241000238631 Hexapoda Species 0.000 claims description 12
- 241000607479 Yersinia pestis Species 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 241000233866 Fungi Species 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 241000221785 Erysiphales Species 0.000 claims description 7
- 239000002917 insecticide Substances 0.000 claims description 7
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
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- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
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- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 3
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- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 3
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- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 238000006116 polymerization reaction Methods 0.000 claims description 3
- HDTRYLNUVZCQOY-UHFFFAOYSA-N α-D-glucopyranosyl-α-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(O)C(O)C(CO)O1 HDTRYLNUVZCQOY-UHFFFAOYSA-N 0.000 claims description 2
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 claims description 2
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- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000005277 alkyl imino group Chemical group 0.000 claims description 2
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- HDTRYLNUVZCQOY-LIZSDCNHSA-N alpha,alpha-trehalose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-LIZSDCNHSA-N 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 2
- 229920002678 cellulose Polymers 0.000 claims description 2
- 239000001913 cellulose Substances 0.000 claims description 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
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- 229940035034 maltodextrin Drugs 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
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Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23B—PRESERVING, e.g. BY CANNING, MEAT, FISH, EGGS, FRUIT, VEGETABLES, EDIBLE SEEDS; CHEMICAL RIPENING OF FRUIT OR VEGETABLES; THE PRESERVED, RIPENED, OR CANNED PRODUCTS
- A23B7/00—Preservation or chemical ripening of fruit or vegetables
- A23B7/14—Preserving or ripening with chemicals not covered by groups A23B7/08 or A23B7/10
- A23B7/153—Preserving or ripening with chemicals not covered by groups A23B7/08 or A23B7/10 in the form of liquids or solids
- A23B7/154—Organic compounds; Microorganisms; Enzymes
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N3/00—Preservation of plants or parts thereof, e.g. inhibiting evaporation, improvement of the appearance of leaves or protection against physical influences such as UV radiation using chemical compositions; Grafting wax
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/12—Quaternary ammonium compounds
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
- A01N43/16—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom
Definitions
- Cationic Polysaccharide Compound as a Fungicide. Pesticide. Algaecide. Dessicant and for extending the Shelf Life of Fruits and Vegetables.
- the invention relates to the use of known cationic polysaccharide compounds as fungicides, pesticides, algaecides, dessicants and for extending the shelf life of fruit and vegetables.
- polyethylenimine biocides for consumer products, coatings, coating compositions and medical devices to prevent growth of microorganisms has been described by US 2011/0171279 Al.
- Polyethylenimine polymers are branched, spherical polymeric amines with a high charge density, which enable them to adsorb tightly on negatively charged surfaces.
- PolyDADMAC diallyldimethyl ammonium chloride
- the molecular weight of commercial polyDADMAC products is typically in the range of hundreds of thousands of grams per mole, and even up to a million for some products.
- W02004/076770 Al describes polyDADMAC as antifungal agents.
- W02005/018326 Al describes amino functionalised fungicidal polymers of typical high molecular weight (preferably 30kDa and more) obtained by polymerization of acrylic monomers to combat phytopathogenic fungi.
- Chitosan a cationic linear polysaccharide composed of randomly distributed b-( I 4)-linked D- glucosamine (deacetylated unit) and N-acetyl-D-glucosamine (acetylated unit), is a natural polymer which has been described for agrochemical uses (e.g. by Abdelbasset El Hadrami et al., Mar. Drugs 2010, 8, 968-987). Being derived from a natural polymer (chitin), chitosan is a non-toxic, biocompatible and biodegradable polymer. The Environmental Protection Agency EPA concluded in 2008 that there are no major identifiable risks to human health of chitin and chitosan products.
- the objective of the present invention has been solved by the use of a cationic polysaccharide compound which contains, per monosaccharide unit, on average at least 0.1 cationic group of the formula:
- A represents a straight-chain or branched C2-C6 alkylene group which is optionally preceded by a carbonyl group or optionally interrupted by one or two oxygen atoms or imino or alkylimino groups and optionally substituted by one or two hydroxyl groups or amine groups or a carboxyl or carbamoyl group; or“A” represents the residue of a monosaccharide unit;
- R 1 and R 2 each represent hydrogen methyl, carboxymethyl, phosphonomethyl, ethyl, hydroxyethyl, propyl, isopropl, allyl, hydroxypropyl or dihydroxypropyl or, together with the nitrogen atom, form a pyrrolidino, piperidino, piperazino, N’-alkylpiperazino, N’-(hydroxyalkyl)piperazino, N’- (aminoalkyl)piperazino, morpholino or hexamethyleneamino group;
- R 3 represents hydrogen, C1-C18 alkyl, C3-C18 alkenyl, alkynyl or cycloalkyl, C4-C18 cycloalkyl-alkyl or C7- Ci 8 aralkyl or a group of the formula -A-Fruc, where“A” has the above-mentioned meaning and“Fruc” represents a polysaccharide residue bonded via oxygen; and
- R 4 represents hydrogen, methyl, ethyl, hydroxyethyl, hydroxypropyl or dihydroxypropyl; where the amine nitrogen atoms can be uncharged or protonated or quarternised with methyl, ethyl, hydroxyethyl, hydroxypropyl or dihydroxypropyl.
- the cationic derivate of the polysaccharide has a solubility in water of at least 20 wt-% at a temperature of 25 °C, preferably at least 30 wt-%.
- Cationic fructan compounds as e.g. described in W098/14482 Al are known to be useful as auxiliaries in papermaking, water treatment, sludge treatment, in cosmetics, as disinfectants, hair conditioners, flocculants, shale inhibitors, corrosion inhibitors, demulsifiers, adhesive textile auxiliaries, or as additives in building, ceramics or plastics.
- agricultural and environmental science uses such as vector control, professional pest control management, forestry, turf and ornamental for cationic fructan compounds have not yet been described.
- the cationic polysaccharide compounds of the invention are easy to formulate as they are not specifically sensitive to certain pH-values.
- a preferred embodiment of the invention relates to the use of a cationic polysaccharide compound which is selected from the group consisting of sucrose, trehalose, lactose, fructan, dextran, maltodextrin, amylose and cellulose and wherein each polysaccharide contains, per monosaccharide unit, on average at least 0.1 cationic group of the formula:
- Another preferred embodiment of the invention relates to the use of a cationic polysaccharide compound which has a cationic group of the formula: -A-N + R 1 R 2 R 3 .
- Another particularly preferred embodiment of the invention relates to the use of a polysaccharide compound which is fructan and which contains, per monosaccharide unit, on average at least 0.1 cationic group of the formula:
- the degree of substitution describes the number of cationic compounds per monosaccharide unit, which relates to the charge density of the cationic polymer.
- Another embodiment of the invention relates to the above described polysaccharide compound which preferably contains, per monosaccharide unit, on average from 0.1 to 2.5, more preferably on average from 0.2 to 2.0 and especially preferred from 0,35 to 1,5 cationic group.
- cationic compounds are understood to be nitrogen compounds which are intrinsically cationic (quaternary ammonium compounds) or which are cationic only in an acid medium (primary, secondary or tertiary amine compounds).
- the natural amines corresponding to the ammonium compounds therefore always fall under the same concept.
- the preferred average chain length for other uses is from 3 to 15 monosaccharide units.
- the polysaccharide compounds are understood to be fructan compounds which are all oligosaccharides and polysaccharides which have a multiplicity of anhydrofructose units. These fructans can have a polydisperse chain length distribution and can be straight-chain or branched.
- the fructans comprise both products obtained directly from a vegetable or other source and products in which the average chain length has been modified (increased or reduced) by fractionation, enzymatic synthesis or hydrolysis.
- the preferred average chain length is at least 8, in particular at least 15 or even at least 25 monosaccharide units.
- the preferred average chain length for other uses is from 3 to 15 monosaccharide units.
- the fructan as used according to the invention contains predominantly b-2,1 bonds, as in inulin (see also Mensink et al., Carbohydrate Polymers 130 (2015) 405-419). Inulin can be obtained from, for example, chicory, dahlias and Jerusalem artichokes.
- fructans such as inulin can be achieved by, for example, low temperature crystallisation (see WO 96/01849 Al), separation by column chromatography (see WO 94/12541 Al), membrane filtration (sec EP-A-440074 A and EP-A-627490 A) or selective precipitation with an alcohol.
- Other fructans such as long-chain fructans which, for example, are obtained on crystallisation, fructans from which monosaccharides and disaccharides have been removed and fructans in which the chain length has been lengthened enzymatically, can also be converted to cationic compounds.
- Prior hydrolysis to obtain shorter fructans can be carried out, for example enzymatically (endoinulinase), chemically (water plus acid) or by heterogenous catalysis (acid ion exchange resin).
- crosslinked fructans can be used for producing cationic compounds.
- Reduced fructans can also be used. Reduced fructans are fructans in which reducing terminal groups (usually fructose groups) have been reduced, for example using sodium borohydride or using hydrogen in the presence of a transition metal catalyst.
- hydroxyalkylated, carboxymethylated and oxidised fructans can also serve as the basis for cationic compounds.
- Hydroxyalkylated and carboxymethylated fructans can be obtained by reaction of the fructan with, respectively, ethylene oxide or another alkylene oxide (see EP-A-638589 A) and chloroacetic acid, preferably in an aqueous medium with a base.
- Oxidised fructans are fructans which have been converted by treatment with, for example, hypochlorite or periodate and/or chlorite into compounds which contain carboxyl and/or aldehyde groups.
- the introduction of cationic groups into fructan compounds containing carboxyl groups leads to amphoteric compounds which have interesting properties.
- a modified inulin which is particularly suitable for conversion to a cationic compound is a reduced dialdehyde-inulin.
- dialdehyde -inulin is reduced, for example with hydrogen in the presence of a transition metal or with sodium borohydride, a polyol (poly-a-hydroxymethyl-a- [2 -hydroxy- 1- (hydroxymethyl) -ethoxy] ethylene oxide) is produced which contains a large number of primary hydroxyl groups. These polyols can be converted to cationic compounds.
- dialdehydeinulin can be reductively animated (in one step or two steps) using conventional reducing agents to produce the polyol indicated above wherein one or more hydroxymethyl groups are replaced by (substituted) aminomethyl groups, which may subsequently be quaternised.
- Amines to be used in the reductive ami nation include ammonia and primary C1-C6 alkylamines and alkylenediamines.
- Examples of straight-chain or branched C2-C6 alkylene groups which are optionally preceded by a carbonyl group or optionally interrupted by one or two oxygen atoms or optionally alkylated and/or protonated imino groups and which are optionally substituted by one or two hydroxyl groups or amine groups or a carboxyl or carbamoyl group are ethylene, 1, 2-propylene, 1, 3-propylene, 2-hydroxy- 1,3- propylene, tetramethylene, hexamethylene, 2, 2-dimethyl-l, 3-propylene, 2-butenylene, 2-butynylene, 2,4- hexadienylene, cyclohexylene, N-methyliminodiethylene, diiminotriethylene, oxydiethylene, oxydipropylene, ethyleneiminocarbonylmethylene, carbonylethylene and carboxy ethylene.
- a preferred embodiment of the invention relates to the above described polysaccharide compound, wherein the polysaccharide compound is characterized in that“A” is bonded to an oxygen atom of the monosaccharide unit.
- Another preferred embodiment relates to the above described polysaccharide compound, wherein the polysaccharide compound is characterized in that R 1 and R 2 each represent methyl or ethyl.
- a further preferred embodiment relates to the above described frutan compound, wherein the polysaccharide compound is characterized in that“A” represents ethylene or 2-hydroxypropylene.
- the polysaccharide compound as used according to the invention are further characterized in that R 1 , R 2 and R 3 each represent methyl or ethyl.
- “A” represents a 2-hydroxy- 1,3 -propylene group.
- cationic polysaccharide resp. fructan compounds are based on inulin, i.e. chemically modified cationic inulin and particularly preferred hydroxypropyl trimonium inulin (CAS-no. 205131-94-8), which is commercially available.
- Cosun Biobased Products for example offers a series of cationic inulines with different degree of substitution or varying charge density under their tradename QUATIN.
- bio-sourced and chemically enhanced products come as aqueous solutions with high solid contents (>35 w% active material), are inherent biodegradable, not classified as hazardous and are not toxic to aquatic life.
- cationic fructan compounds can be prepared according to known processes such as e.g. described in detail in WO 98/14482 Al.
- Cationic polysaccharide preferably fructan compounds containing groups of formula -A-N + R 1 R 2 R 3 , where“A” represents ethylene or 1, 2-propylene
- Cationic polysaccharide preferably fructan compounds containing groups of formula -A-N + R 1 R 2 R 3 , where“A” represents ethylene or 1, 2-propylene
- the reaction can be carried out with a glycidylamine or a 3-halo-2-hydroxypropylamine or a corresponding ammonium salt.
- the reaction can be carried out with a 2-dialkylamino-3-halopropionamide or 2-dialkylamino-3-halopropionic acid.
- 2-butenylene an unsubstituted or substituted 4-chloro-2-butenylamine can be used.
- Suitable reagents are 2-chloropropyldimethylamine, N-(2-chloroethyl)-morpholine, 3-bromopropyl- trimethylammonium bromide, chloroethyldiethylamine, 4-chloro-l -methyl-piperidine, and the like.
- the polysaccharide (preferably fructan) compounds can also be obtained by reaction of the polysaccharide (preferably fructan) with an alkylene oxide to give a hydroxyalkylpolysaccharide (preferably a hydroxyalkylfructan) with a high degree of substitution, followed by reaction with a b- haloamine of the formula X-CH 2 -CH-N + R 1 R 2 R 3 .
- One of the nitrogen atoms in the iminocarbamoyl group can have been protonated or have been quaternised, for example with methyl.
- Polysaccharide (preferably fructan) compounds of the above-mentioned formula in which R 3 represents - A-Fruc are cross-linked derivatives which can be obtained by reaction of the polysaccharide (preferably fructan) with an amine containing two or three coupling functional groups, such as N,N-bis- or N,N,N- tris-(2-chloroethyl)amine, N,N-bis- or N,N,N-tris-(3-chloro-2-hydroxypropyl)amine and N,N’-bis(2- chloroethyl)piperazine. Any 2-chloroethyl or 3-chloro-2-hydroxypropyl groups remaining after the coupling reaction can simply be hydrolysed to 2-hydroxyethyl or 2,3-dihydroxypropyl groups, respectively.
- an amine containing two or three coupling functional groups such as N,N-bis- or N,N,N- tris-(2-chloroethyl)amine, N,N-bis- or
- reaction for example 0.1 - 10 equivalents, in particular 0.2 - 5 equivalents, of the amine reagent concerned, which equivalents are based on the number of monosaccharide units (for fructan preferably the anhydrofructose units in the fructan).
- the reaction can be carried out at room temperature, but preferably at an elevated temperature of 30° - 150° C.
- the reaction times are usually between a few minutes and a few hours, depending on the temperature. After the reaction has gone to completion, the reaction mixture is neutralised and, partly depending on the intended use, worked up.
- the polysaccharide preferably the fructan
- the polysaccharide compound has to be free from salts and residual reagent or hydrolysis products thereof (such as hydroxyalkylamines) for the intended use
- known purification techniques can be used such as electrodialysis, nanofrltration and precipitation with an alcohol, such as ethanol.
- a particularly advantageous process for preparing the present polysaccharide (preferably fructan) derivatives involves a reaction carried out under conditions of elevated temperature, intensive kneading and a small amount of solvent, such as those which prevail in an extrusion reactor.
- An example of such conditions for the preparation of starch derivatives is described by Meuser et al., Starch/Staerke 42 (1990), 330-360.
- an extrution preparation method it is possible, for example to meter the polysaccharide (preferably fructan) into the extruder in solid form and, in addition, to meter the base (sodium hydroxide solution) and amine reagent (for example 3-chloro-2-hydroxypropyl-trimethylammonium chloride) into the extruder in the form of a concentrated solution.
- the solids content is preferably greater than 25 % and in particular greater than 50 % up to close to 100 %.
- the temperature can, for example, be chosen between 60° and 150° C. Under these conditions a significant shortening of the reaction time is obtained and, furthermore, high efficiency is achieved.
- the cationic polysaccharide (preferably fructan) compounds can then be further modified.
- the neutral amines can be converted to the acid addition salts, such as hydrochlorides, hydrobromides, sulphates, phosphates acetates and the like.
- Derivatives containing a primary, secondary or tertiary amine group can be converted to further N-alklated and optionally quaternary derivatives using conventional alkylating agents such as dimethyl sulphate, ethyl bromide, chloroethanol, alkyl chloride, benzyl chloride, and the like.
- cationic polysaccharide (preferably fructan) compounds as used according to the invention are also possible, such as oxidation with, for example, hypochlorite, periodic acid or hydrogen peroxide, carboxyl groups being formed.
- the derivatives can also be carboxymethylated with, for example, chloroacetic acid or sulphoalkylated with, for example, propylene sulphone.
- Such modifications are preferably carried out in such a way that the degree of substitution by the groups introduced in this way, such as carboxyl groups, is lower than the degree of substitution by amine or ammonium groups.
- fungicide means the capacity of a substance to increase the mortality or inhibit the growth rate of fungi.
- the cationic polysaccharide compounds of the invention are preferably used to curatively or preventively (preferably at least preventively) control phytopathogenic fungi wherein the use comprises applying to the plant, to a part of the plant and/or to a locus of the plant the cationic polysaccharide compounds of the invention.
- phytopathogenic fungi stands for all fungal and chromista organisms which cause damages on plants or any part of a plant.
- fungal organisms are Ascomycota, Basidiomycota, Chytridiomycota, Deuteromycota, Glomeromycota, Microsporidia, Zygomycota, and anamorphic fungi.
- Chromista are Oomycota.
- the cationic polysaccharide compounds of the invention are used to curatively or preventively control Ascomycota.
- Powdery Mildew Diseases such as Blumeria diseases caused for example by Blumeria graminis; Podosphaera diseases caused for example by Podosphaera leucotricha; Sphaerotheca diseases caused for example by Sphaerotheca fuliginea; Uncinula diseases caused for example by Uncinula necator; Rust Diseases such as Gymnosporangium diseases caused for example by Gymnosporangium sabinae; Hemileia diseases caused for example by Hemileia vastatrix; Phakopsora diseases caused for example by Phakopsora pachyrhizi and Phakopsora meibomiae; Puccinia diseases caused for example by Puccini a recondite, and Puccinia triticina; Uromyces diseases caused for example by Uromyces appendiculatus; Oomycete Diseases such as Bremia diseases caused for example by Bremia lactucae; Peronospora diseases caused for example by Per
- Plants or parts thereof to be treated with the cationic polysaccharide compound of the invention are preferably selected from the group consisting of citrus, pome fruits, stone fruits, tropical fruits, nuts, oilseed rape, berries, vegetables; cereals such as wheat, barley, oats, rye; cotton, sunflower, grape, tea, coffee, maize, rice; legumes including lentils, garbanzos and soybean, ornamentals and turf.
- Citrus is a common term and genus (Citrus) of flowering plants in the rue family, Rutaceae.
- the term Citrus includes orange (C. sinensis), lemon (C. limon), grapefruit (C. paradisi), and lime (various, mostly C. aurantifolia, the key lime).
- Pome is a common term for fruits produced by flowering plants in the subtribe Malinae of the family Rosaceae and for plants producing these fruits.
- a pome is an accessory fruit composed of one or more carpels surrounded by accessory tissue. Examples of plants that produce fruit classified as a pome are apple, loquat, pear, Pyracantha, and quince.
- Vegetable refers to an edible plant or its part selected from the list consisting of flower bud vegetable such as broccoli, cauliflower, globe artichokes and capers; leaf vegetable such as kale, spinach (Spinacia oleracea), arugula (Eruca sativa), and lettuce (Lactuca sativa); stem vegetable such as kohlrabi; stem shoot vegetable such as asparagus, bamboo shoots, potatoes (Solanum tuberosum L) and sweet potatoes (Ipomoea batatas); root vegetable such as carrots (Daucus carota), parsnips (Pastinaca sativa), beets (Beta vulgaris), and radishes (Raphanus sativus); bulb vegetable such as onion, garlic and shallots of genus Allium; tomato (Solanum lycopersicum), cucumber (Cucumis sativus), zucchini, squash and pumpkin of genus species Cucurbita pepo, pepper (of family Solanaceae),
- Stone fruit are all species of the Prunus genus.
- plants that produce fruit classified as a stone fruit are e.g. peaches, nectarines, plums, apricots, and cherries.
- Subtropical and tropical fruit are fruit produced by plants native to the geographical and climatic region of the subtropics or tropics.
- plants that produce fruit classified as a subtropical or tropical fruit are e.g avocado, banana, cherimoya, date, dragon fruit, durian, fig, guava, jackfruit, kiwi, lychee, mango, mangosteen, passion fruit, papaya, pineapple, persimmon, pomegranate, rambutan and star fruit.
- Nuts are referring to any hard-walled, edible kernel such as e.g. almonds, Brazil nuts, cashews, hazelnuts, macadamias, peanuts, pecans, pine nuts, pistachios and walnuts.
- Berries are any small edible fruit usually juicy, round, brightly coloured, sweet or sour, and do not have a stone or pit, although seeds may be present as e.g. blackberry, blueberry, cranberry, currant, elderberry, gooseberry, grape, raspberry, strawberry.
- Ornamentals are plants grown for decorative purposes in gardens and landscape design, as houseplants, for cut flowers and specimen display, e.g. roses, chrysanthemums, tulips, etc.
- the cationic polysaccharide compounds are used to curatively or preventively (preferably at least preventively) control powdery mildew.
- pests refers to the capacity of a substance to kill or cause a knockdown of a pest.
- the cationic polysaccharide compounds of the invention are active against normally sensitive and resistant species and against all or some stages of development.
- the abovementioned pests include:
- Pests from the phylum of the Arthropoda in particular from the class of the Arachnida, for example Acarus spp., for example Acarus siro, Aceria kuko, Aceria sheldoni, Aculops spp., Aculus spp., for example Aculus fockeui, Aculus pointedendali, Amblyomma spp., Amphitetranychus viennensis, Argas spp., Boophilus spp., Brevipalpus spp., for example Brevipalpus phoenicis, Bryobia graminum, Bryobia praetiosa, Centruroides spp., Chorioptes spp., Dermanyssus gallinae, Dermatophagoides pteronyssinus, Dermatophagoides farinae, Dermacentor spp., Eotetranychus spp., for example Eote
- Nephotettix spp. Myzus nicotianae, Nasonovia ribisnigri, Neomaskellia spp., Nephotettix spp., for example Nephotettix cincticeps,, Nephotettix nigropictus, Nettigoniclla spectra, Nilaparvata lugens, Oncometopia spp., Orthezia praelonga, Oxya chinensis, Pachypsylla spp., Parabemisia myricae, Paratrioza spp., for example Paratrioza cockerelli, Parlatoria spp., Pemphigus spp., for example Pemphigus bursarius, Pemphigus populivenae, Peregrinus maidis, Perkinsiella spp., Phenacoccus spp., for example Phenacoccus madeirensis, Phloeomy
- phytoparasitic nematodes in particular Aglenchus spp., for example Aglenchus agricola, Anguina spp., for example Anguina tritici, Aphelenchoides spp., for example Aphelenchoides arachidis, Aphelenchoides fragariae, Belonolaimus spp., for example Belonolaimus gracilis, Belonolaimus longicaudatus, Belonolaimus nortoni, Bursaphelenchus spp., for example Bursaphelenchus cocophilus, Bursaphelenchus eremus, Bursaphelenchus xylophilus, Cacopaurus spp., for example Cacopaurus pestis, Criconemella spp., for example Criconemella curvata, Criconemella onoensis, Criconemella ornata, Criconemella rusium, Criconemella
- the term “pesticide” according to the present invention refers to an “insecticide”.
- insecticide refers to the capacity of a substance to kill or cause a knockdown of an insect.
- flies such as filth flies or housefly and its relatives (Muscidae); flesh flies (Sarcophagidae); bottle flies and blowflies (Calliphorid
- the cationic polysaccharide compounds of the invention directly on the pests resp. the target insects e.g. with a direct spray application.
- Target insect is an insect that is naturally attracted to the area of interest and for which it is desired to implement a measure of population control.
- target insect encompasses the insect at all stages of development and its offspring, including the mature insect, eggs, pupae stage, and larvae.
- algaecide refers to characteristics of the cationic polysaccharide compounds of the invention to curatively or preventively control algae and/or moss growth.
- Another embodiment of the invention relates to the use of the cationic polysaccharide compounds according to the invention as a (preferably preharvest) dessicant or defoliant.
- This refers to the capability of the cationic polysaccharide compounds of the invention to dry up, cause to dry up, deprive, or exhaust the moisture in certain crops such as maize, cereals, oilseed rapes, legumes, potatoes, cotton.
- Another embodiment relates to the use of the cationic polysaccharide compounds of the invention to extend the shelf life of fruits and vegetables.
- the cationic polysaccharide compounds of the invention are applied to the crop prior to the harvest of the fruits and vegetables, however, postharvest applications are also possible.
- the fruits are preferably selected from the group consisting of banana, blackcurrant, redcurrant, gooseberry, tomato, eggplant, guava, lucuma, chili pepper, pomegranate, kiwifruit, grape, table grapes pumpkin, gourd, cucumber, melon, orange, lemon, lime, grapefruit, cranberry, blueberry, blackberry, raspberry, boysenberry, hedge apple, pineapple, fig, mulberry, apple, apricot, peach, cherry, sunflower seed, strawberry and plum.
- the vegetables are preferably selected from the group consisting of broccoli, green bean, lettuce, cauliflower, globe artichokes, sweeteorn, maize, kale, collard greens, spinach, beet greens, turnip greens, endive; leeks, Brussels sprouts, celery, rhubarb, asparagus, ginger; potatoes, Jerusalem artichokes, sweet potato, yarn bean sprouts, carrots, parsnips, beets, radishes, turnips, onions, garlic, shallots.
- the application rates can be varied within a broad range, depending on the type of application.
- the application rates are generally ranging from 1 to 50 liter/ha, more preferably from 5 to 30 liter/ha, most preferably from 7 to 20 liter/ha based upon the pure a.s. (active substance).
- the cationic polysaccharide compounds of the invention can be applied to all parts of the plants such as shoot, leaf, flower and root, leaves, needles, stalks, stems, flowers, vegetative buds and flower buds fruiting bodies and fruits.
- the terms“extending the shelf life” refers to a period of at least 1 day, preferably at least 2 days, even more preferably at least 1 week wherein the overall quality of a fruit and/or vegetable can be maintained in comparison to an untreated fruit and/or vegetable.
- the treatment of the plants and pests is carried out directly by the customary treatment methods, for example by spraying, immersion, vaporizing, fogging, injecting, dripping, drenching, broadcasting or painting.
- the cationic polysaccharide compounds of the invention are applied via spraying.
- the cationic polysaccharide compounds of the invention can be converted to customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, very fine capsules in polymeric substances and in coating compositions for seed, and also ULV cold-and warm-fogging formulations. These formulations are produced in a known manner.
- a commercial aqueous solution of cationic polyethyleneimine (Lupasol® HF) was obtained from BASF.
- Breakthru® S240 a polyalkyleneoxide modified peptamethyltrisiloxane from Evonik
- Breakthru® S240 was also tested on its own. That is without a test product as mixing partner.
- a commercial sulphur based and contact active product (SUFRAN JET® WG 80) was employed as a bench mark with its recommended rate.
- the spray solution was prepared by diluting the recommended amount in tap water (l,5g/L). The spray solutions were applied with a manual pump sprayer with a spray volume of lOOOL/ha to visible coverage of the upper leaf surface.
- Leaves were treated with the test samples prior to inoculation with a fungal pathogen. 24 hours after the application one half side along the middle vein of each treated leaf was artificially inoculated with spores of Powdery Mildew ( Sphaerothecafuliginea ) at a density of 10000 spores/ml.
- Powdery Mildew Sphaerothecafuliginea
- the inoculated leaf side was assessed visually 11 days after inoculation for % leaf area showing mycelium growth.
- the % control was calculated using the formula of Abbott (ABBOTT, W.S. (1925): A method of computing the effectiveness of an insecticide. Journal of economic Entomology, 18, 265-267).
- Control % (l-(value in treated/value in untreated))*l00
- the tank mix component Breakthru S240 alone (treatment line 2) had did not provide any control of the development of the fungal pathogen.
- the test samples FL2, FL3, FL4, F16 - each combined with the tankmix components Breakthru S240 - achieved control levels of 100%, 70%, 97% and 97%, respectively.
- the commercial reference product (Sufran Jet WG 80) provided 100% control.
- Breakthru® S240 Evonik
- Breakthru® S240 was also tested on its own. That is without a test product as mixing partner.
- the trial in example 2 showed strong disease pressure with the infested leaf area increasing from 0% at time of application to 35% on day 8 after inoculation to 81% on day 13.
- the tank mix component Breakthru S240 alone (treatment line 2) had a minor effect on the development of the fungal pathogen of 44 and 32% control at 8 and 13 days after inoculation, respectively.
- the Quatin test samples achieved control levels of 90% and 98% (8 days after inoculation), 89% and 95% (13 days after inoculation), 92% and 96% (21 days after inoculation), respectively.
- the commercial reference product (Sufran Jet) provided 100% control at the same dates.
Abstract
Description
Claims
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PCT/EP2019/070449 WO2020025592A1 (en) | 2018-07-31 | 2019-07-30 | Use of a cationic polysaccharide compound as a fungicide, pesticide, algaecide, dessicant and for extending the shelf life of fruits and vegetables |
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DE4003140A1 (en) | 1990-02-02 | 1991-08-08 | Suedzucker Ag | METHOD FOR THE PRODUCTION OF A GLUCOSE, FRUCTOSE AND SACCHAROSEARM INULOOLIGOSACCHARIDE PRODUCT |
BE1006377A3 (en) | 1992-11-24 | 1994-08-09 | Raffinerie Tirlemontoise Sa | SEPARATION METHOD OF polydispersed composition SACCHARIDES, PRODUCTS OBTAINED BY THE METHOD AND USE OF PRODUCTS OBTAINED IN FOOD COMPOSITIONS. |
DE4316425C2 (en) | 1993-05-17 | 1998-05-20 | Suedzucker Ag | Process for the production of long-chain inulin, the inulin thus produced and its use |
EP0792889B1 (en) | 1993-08-10 | 2000-12-27 | Südzucker Aktiengesellschaft Mannheim/Ochsenfurt | Use of inulin derivatives |
ATE184290T1 (en) | 1994-07-07 | 1999-09-15 | Tiense Suikerraffinaderij Nv | FRACTIONATED POLYDISPERSE COMPOSITIONS |
DK0822943T3 (en) | 1995-04-27 | 1999-11-29 | Cooperatie Cosun U A | inulin |
NL1003776C2 (en) | 1996-08-09 | 1998-02-20 | Cooperatie Cosun U A | Environmentally friendly heavy metal complexants |
NL1004153C2 (en) | 1996-09-30 | 1998-03-31 | Cooperatie Cosun U A | New fructan derivatives. |
US6534075B1 (en) * | 1999-03-26 | 2003-03-18 | Ecolab Inc. | Antimicrobial and antiviral compositions and treatments for food surfaces |
WO2004076770A1 (en) | 2003-02-25 | 2004-09-10 | Quick-Med Technologies, Inc. | Improved antifungal gypsum board |
GB0319506D0 (en) | 2003-08-19 | 2003-09-17 | Syngenta Ltd | Fungicidal method |
US20110171279A1 (en) | 2009-11-02 | 2011-07-14 | Ndsu Research Foundation | Polyethylenimine biocides |
CN103875669B (en) * | 2013-04-07 | 2015-05-20 | 海南正业中农高科股份有限公司 | Bactericidal composition containing cyflufenamid and chitosan oligosaccharide |
FR3006314B1 (en) * | 2013-05-31 | 2016-07-01 | Sipre | NOVEL METHOD FOR THE SYNTHESIS OF N-ALKYL-GLYCOSYL (DI) AMINE DERIVATIVES AND THEIR APPLICATIONS |
US20190125896A1 (en) * | 2016-04-14 | 2019-05-02 | Mirexus Biotechnologies Inc. | Anti-infective compositions comprising phytoglycogen nanoparticles |
ES2778624T3 (en) * | 2016-10-31 | 2020-08-11 | Coöperatie Koninklijke Cosun Ua | Detergent composition comprising a cationic derivative of a polysaccharide |
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